NPASS Compound

Structure

CID54468 OpenBabel06191715392D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.2704 2.5734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0589 -1.4437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0324 1.2190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2389 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6320 0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6195 -0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1195 1.4985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0533 -1.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3600 1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4928 -2.3447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6195 -0.6922 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2185 1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2430 0.0896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9960 0.0896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8789 1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3930 0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0204 1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9295 -3.1709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9685 2.5734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3680 1.1420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4900 -2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 10 1 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 11 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 8 1 1 0 0 0 11 13 1 0 0 0 0 12 7 1 6 0 0 0 12 14 1 0 0 0 0 13 17 1 6 0 0 0 14 6 1 1 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.15
Volume:	310.324
LogP:	1.742
LogD:	1.797
LogS:	-2.426
# Rotatable Bonds:	3
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.577
Synthetic Accessibility Score:	4.32
Fsp3:	0.706
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	6.252543971640989e-05
Pgp-inhibitor:	0.231
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	68.04183197021484%
Volume Distribution (VD):	0.561
Pgp-substrate:	40.87955093383789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.147
CYP2C19-substrate:	0.547
CYP2C9-inhibitor:	0.157
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.535
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	7.645
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.571
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.738
Skin Sensitization:	0.925
Carcinogencity:	0.751
Eye Corrosion:	0.919
Eye Irritation:	0.937
Respiratory Toxicity:	0.85

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC54468

Natural Product ID:	NPC54468
*Common Name:**	(1S,5S,7R,8S,10R)-14-Acetoxy-4-Oxopseudoguai-11(13)-En-12,8-Olide
IUPAC Name:	[(3aS,5R,5aS,8aS,9aR)-8a-methyl-1-methylidene-2,8-dioxo-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-5-yl]methyl acetate
Synonyms:
Standard InCHIKey:	UGZPAZLOJSSVQY-WLZFUECHSA-N
Standard InCHI:	InChI=1S/C17H22O5/c1-9-12-7-17(3)13(4-5-15(17)19)11(8-21-10(2)18)6-14(12)22-16(9)20/h11-14H,1,4-8H2,2-3H3/t11-,12+,13-,14-,17-/m0/s1
SMILES:	CC(=O)OC[C@@H]1C[C@@H]2OC(=O)C(=C)[C@H]2C[C@]2([C@H]1CCC2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911130
PubChem CID:	54671715
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0002046] Ambrosanolides and secoambrosanolides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21894898]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[21894898]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6600.0	nM	PMID[476006]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC54468 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	2035
0.2-0.3	8133
0.3-0.4	15275
0.4-0.5	8414
0.5-0.6	6119
0.6-0.7	2035
0.7-0.8	333
0.8-0.85	64
0.85-0.9	24
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC238593
0.961	High Similarity	NPC293418
0.961	High Similarity	NPC73052
0.961	High Similarity	NPC290508
0.9221	High Similarity	NPC208223
0.9114	High Similarity	NPC6823
0.9059	High Similarity	NPC191339
0.9059	High Similarity	NPC286341
0.9048	High Similarity	NPC168679
0.9048	High Similarity	NPC12872
0.8916	High Similarity	NPC236692
0.8916	High Similarity	NPC309757
0.8889	High Similarity	NPC246076
0.8831	High Similarity	NPC143979
0.8831	High Similarity	NPC320537
0.881	High Similarity	NPC118601
0.881	High Similarity	NPC24728
0.8736	High Similarity	NPC153590
0.8706	High Similarity	NPC471149
0.8706	High Similarity	NPC178875
0.8652	High Similarity	NPC91771
0.8652	High Similarity	NPC142529
0.8621	High Similarity	NPC123177
0.8621	High Similarity	NPC70595
0.8621	High Similarity	NPC74103
0.8621	High Similarity	NPC150978
0.8605	High Similarity	NPC283409
0.8588	High Similarity	NPC201658
0.8571	High Similarity	NPC161957
0.8537	High Similarity	NPC47635
0.8523	High Similarity	NPC200237
0.8523	High Similarity	NPC473263
0.8523	High Similarity	NPC473273
0.8523	High Similarity	NPC60386
0.8523	High Similarity	NPC308656
0.8523	High Similarity	NPC473234
0.8506	High Similarity	NPC54065
0.8506	High Similarity	NPC297474
0.8506	High Similarity	NPC253144
0.8471	Intermediate Similarity	NPC64153
0.8471	Intermediate Similarity	NPC304558
0.8427	Intermediate Similarity	NPC473331
0.8415	Intermediate Similarity	NPC69271
0.8415	Intermediate Similarity	NPC74673
0.8415	Intermediate Similarity	NPC51507
0.8409	Intermediate Similarity	NPC35959
0.8409	Intermediate Similarity	NPC133888
0.8409	Intermediate Similarity	NPC293001
0.8409	Intermediate Similarity	NPC171360
0.8409	Intermediate Similarity	NPC63193
0.8409	Intermediate Similarity	NPC29821
0.8409	Intermediate Similarity	NPC284185
0.8409	Intermediate Similarity	NPC57304
0.8391	Intermediate Similarity	NPC155935
0.8372	Intermediate Similarity	NPC270270
0.8333	Intermediate Similarity	NPC39588
0.8333	Intermediate Similarity	NPC215294
0.8333	Intermediate Similarity	NPC163228
0.8313	Intermediate Similarity	NPC10276
0.8313	Intermediate Similarity	NPC35089
0.8312	Intermediate Similarity	NPC5714
0.8295	Intermediate Similarity	NPC35809
0.8293	Intermediate Similarity	NPC469620
0.8293	Intermediate Similarity	NPC182550
0.828	Intermediate Similarity	NPC171759
0.8276	Intermediate Similarity	NPC207114
0.8276	Intermediate Similarity	NPC217983
0.8256	Intermediate Similarity	NPC107787
0.8256	Intermediate Similarity	NPC56593
0.8235	Intermediate Similarity	NPC115786
0.8193	Intermediate Similarity	NPC276356
0.8182	Intermediate Similarity	NPC472872
0.8152	Intermediate Similarity	NPC169205
0.8152	Intermediate Similarity	NPC170143
0.8152	Intermediate Similarity	NPC108475
0.8152	Intermediate Similarity	NPC213947
0.814	Intermediate Similarity	NPC21471
0.814	Intermediate Similarity	NPC78089
0.814	Intermediate Similarity	NPC235792
0.814	Intermediate Similarity	NPC33570
0.8132	Intermediate Similarity	NPC48803
0.8132	Intermediate Similarity	NPC476053
0.8132	Intermediate Similarity	NPC275960
0.8132	Intermediate Similarity	NPC90121
0.8132	Intermediate Similarity	NPC193645
0.8118	Intermediate Similarity	NPC245665
0.8111	Intermediate Similarity	NPC135776
0.8095	Intermediate Similarity	NPC301477
0.8095	Intermediate Similarity	NPC25684
0.8095	Intermediate Similarity	NPC281949
0.809	Intermediate Similarity	NPC19087
0.8072	Intermediate Similarity	NPC469690
0.8068	Intermediate Similarity	NPC79549
0.8065	Intermediate Similarity	NPC141191
0.8065	Intermediate Similarity	NPC54843
0.8049	Intermediate Similarity	NPC476794
0.8049	Intermediate Similarity	NPC470240
0.8046	Intermediate Similarity	NPC104961
0.8046	Intermediate Similarity	NPC470242
0.8046	Intermediate Similarity	NPC70555
0.8046	Intermediate Similarity	NPC70422
0.8046	Intermediate Similarity	NPC187661
0.8043	Intermediate Similarity	NPC18019
0.8043	Intermediate Similarity	NPC185553
0.8043	Intermediate Similarity	NPC24956
0.8023	Intermediate Similarity	NPC224386
0.8023	Intermediate Similarity	NPC194859
0.8	Intermediate Similarity	NPC184063
0.8	Intermediate Similarity	NPC221282
0.7978	Intermediate Similarity	NPC288699
0.7978	Intermediate Similarity	NPC38392
0.7978	Intermediate Similarity	NPC215556
0.7976	Intermediate Similarity	NPC302426
0.7976	Intermediate Similarity	NPC223904
0.7957	Intermediate Similarity	NPC311904
0.7957	Intermediate Similarity	NPC471150
0.7955	Intermediate Similarity	NPC190753
0.7931	Intermediate Similarity	NPC300082
0.7931	Intermediate Similarity	NPC284534
0.7931	Intermediate Similarity	NPC204105
0.7889	Intermediate Similarity	NPC62815
0.7889	Intermediate Similarity	NPC216284
0.7882	Intermediate Similarity	NPC255580
0.7882	Intermediate Similarity	NPC39411
0.7875	Intermediate Similarity	NPC470243
0.7849	Intermediate Similarity	NPC126156
0.7841	Intermediate Similarity	NPC469676
0.7831	Intermediate Similarity	NPC65603
0.7816	Intermediate Similarity	NPC156485
0.7816	Intermediate Similarity	NPC470011
0.7816	Intermediate Similarity	NPC219011
0.7805	Intermediate Similarity	NPC138408
0.7805	Intermediate Similarity	NPC226669
0.7805	Intermediate Similarity	NPC193351
0.7802	Intermediate Similarity	NPC155215
0.7802	Intermediate Similarity	NPC133698
0.7802	Intermediate Similarity	NPC475925
0.7792	Intermediate Similarity	NPC157518
0.7791	Intermediate Similarity	NPC173609
0.7789	Intermediate Similarity	NPC186861
0.7778	Intermediate Similarity	NPC268298
0.7778	Intermediate Similarity	NPC32922
0.7765	Intermediate Similarity	NPC474981
0.7753	Intermediate Similarity	NPC186148
0.7742	Intermediate Similarity	NPC280877
0.7742	Intermediate Similarity	NPC475900
0.7742	Intermediate Similarity	NPC472873
0.7742	Intermediate Similarity	NPC167893
0.7727	Intermediate Similarity	NPC110405
0.7717	Intermediate Similarity	NPC258216
0.7717	Intermediate Similarity	NPC472874
0.7717	Intermediate Similarity	NPC475700
0.7708	Intermediate Similarity	NPC477950
0.7701	Intermediate Similarity	NPC272814
0.7701	Intermediate Similarity	NPC194637
0.7701	Intermediate Similarity	NPC128246
0.7701	Intermediate Similarity	NPC474472
0.7701	Intermediate Similarity	NPC128429
0.7701	Intermediate Similarity	NPC257358
0.7692	Intermediate Similarity	NPC129419
0.7683	Intermediate Similarity	NPC469641
0.7683	Intermediate Similarity	NPC469643
0.7674	Intermediate Similarity	NPC141810
0.7674	Intermediate Similarity	NPC38642
0.7674	Intermediate Similarity	NPC126248
0.7667	Intermediate Similarity	NPC177629
0.7667	Intermediate Similarity	NPC224652
0.7667	Intermediate Similarity	NPC58219
0.7667	Intermediate Similarity	NPC53158
0.766	Intermediate Similarity	NPC476009
0.7653	Intermediate Similarity	NPC203659
0.7647	Intermediate Similarity	NPC617
0.7647	Intermediate Similarity	NPC19841
0.764	Intermediate Similarity	NPC284902
0.764	Intermediate Similarity	NPC67493
0.7634	Intermediate Similarity	NPC198853
0.7634	Intermediate Similarity	NPC477131
0.7634	Intermediate Similarity	NPC127019
0.7634	Intermediate Similarity	NPC167219
0.7629	Intermediate Similarity	NPC225353
0.7619	Intermediate Similarity	NPC195785
0.7619	Intermediate Similarity	NPC122264
0.7619	Intermediate Similarity	NPC15975
0.7614	Intermediate Similarity	NPC470238
0.7614	Intermediate Similarity	NPC138647
0.7609	Intermediate Similarity	NPC290651
0.7609	Intermediate Similarity	NPC131209
0.7604	Intermediate Similarity	NPC471381
0.759	Intermediate Similarity	NPC155587
0.759	Intermediate Similarity	NPC471491
0.7586	Intermediate Similarity	NPC226988
0.7582	Intermediate Similarity	NPC117405
0.7582	Intermediate Similarity	NPC52198
0.7582	Intermediate Similarity	NPC4986
0.7582	Intermediate Similarity	NPC92974
0.7579	Intermediate Similarity	NPC474313
0.7556	Intermediate Similarity	NPC237540
0.7556	Intermediate Similarity	NPC175293
0.7556	Intermediate Similarity	NPC231889
0.7556	Intermediate Similarity	NPC475703

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC54468 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	2780
0.2-0.3	3903
0.3-0.4	1524
0.4-0.5	372
0.5-0.6	234
0.6-0.7	42
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8132	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1695	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7128	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6008	Approved
0.6827	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6435	Approved
0.6804	Remote Similarity	NPD6399	Phase 3
0.6737	Remote Similarity	NPD6903	Approved
0.6702	Remote Similarity	NPD7521	Approved
0.6702	Remote Similarity	NPD7334	Approved
0.6702	Remote Similarity	NPD6409	Approved
0.6702	Remote Similarity	NPD6684	Approved
0.6702	Remote Similarity	NPD7146	Approved
0.6702	Remote Similarity	NPD5330	Approved
0.6702	Remote Similarity	NPD5786	Approved
0.6636	Remote Similarity	NPD6371	Approved
0.663	Remote Similarity	NPD5209	Approved
0.6596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5363	Approved
0.6593	Remote Similarity	NPD5368	Approved
0.6562	Remote Similarity	NPD6672	Approved
0.6562	Remote Similarity	NPD5737	Approved
0.6562	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5362	Discontinued
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8035	Phase 2
0.6531	Remote Similarity	NPD5693	Phase 1
0.6531	Remote Similarity	NPD8034	Phase 2
0.6522	Remote Similarity	NPD5369	Approved
0.65	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4269	Approved
0.6452	Remote Similarity	NPD4270	Approved
0.6429	Remote Similarity	NPD5207	Approved
0.64	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD6053	Discontinued
0.6355	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD4225	Approved
0.6296	Remote Similarity	NPD7320	Approved
0.6296	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD6881	Approved
0.6296	Remote Similarity	NPD6011	Approved
0.6273	Remote Similarity	NPD6650	Approved
0.6273	Remote Similarity	NPD6649	Approved
0.6262	Remote Similarity	NPD5739	Approved
0.6262	Remote Similarity	NPD6402	Approved
0.6262	Remote Similarity	NPD6675	Approved
0.6262	Remote Similarity	NPD7128	Approved
0.6239	Remote Similarity	NPD6012	Approved
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD6014	Approved
0.6239	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD6013	Approved
0.6238	Remote Similarity	NPD7900	Approved
0.6238	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6001	Approved
0.6237	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4252	Approved
0.6222	Remote Similarity	NPD8039	Approved
0.6211	Remote Similarity	NPD7154	Phase 3
0.6204	Remote Similarity	NPD5701	Approved
0.62	Remote Similarity	NPD6411	Approved
0.6186	Remote Similarity	NPD4249	Approved
0.6182	Remote Similarity	NPD7290	Approved
0.6182	Remote Similarity	NPD6883	Approved
0.6182	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD5695	Phase 3
0.6162	Remote Similarity	NPD6080	Approved
0.6162	Remote Similarity	NPD6904	Approved
0.6162	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6146	Remote Similarity	NPD3668	Phase 3
0.614	Remote Similarity	NPD7115	Discovery
0.6126	Remote Similarity	NPD6847	Approved
0.6126	Remote Similarity	NPD6617	Approved
0.6126	Remote Similarity	NPD6869	Approved
0.6126	Remote Similarity	NPD8130	Phase 1
0.6122	Remote Similarity	NPD3573	Approved
0.6122	Remote Similarity	NPD4251	Approved
0.6122	Remote Similarity	NPD4250	Approved
0.6105	Remote Similarity	NPD3667	Approved
0.61	Remote Similarity	NPD46	Approved
0.61	Remote Similarity	NPD6698	Approved
0.61	Remote Similarity	NPD5692	Phase 3
0.6095	Remote Similarity	NPD7639	Approved
0.6095	Remote Similarity	NPD7640	Approved
0.6092	Remote Similarity	NPD229	Approved
0.6082	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8297	Approved
0.6071	Remote Similarity	NPD6882	Approved
0.6068	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5777	Approved
0.6064	Remote Similarity	NPD4819	Approved
0.6064	Remote Similarity	NPD4822	Approved
0.6064	Remote Similarity	NPD4821	Approved
0.6064	Remote Similarity	NPD4820	Approved
0.6061	Remote Similarity	NPD5208	Approved
0.6058	Remote Similarity	NPD6083	Phase 2
0.6058	Remote Similarity	NPD6084	Phase 2
0.6058	Remote Similarity	NPD7902	Approved
0.6042	Remote Similarity	NPD5332	Approved
0.6042	Remote Similarity	NPD4788	Approved
0.6042	Remote Similarity	NPD5331	Approved
0.604	Remote Similarity	NPD6079	Approved
0.604	Remote Similarity	NPD5281	Approved
0.604	Remote Similarity	NPD5694	Approved
0.604	Remote Similarity	NPD6050	Approved
0.604	Remote Similarity	NPD5284	Approved
0.6022	Remote Similarity	NPD4268	Approved
0.6022	Remote Similarity	NPD4271	Approved
0.602	Remote Similarity	NPD6098	Approved
0.602	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5982	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5211	Phase 2
0.598	Remote Similarity	NPD5779	Approved
0.598	Remote Similarity	NPD5778	Approved
0.5979	Remote Similarity	NPD4786	Approved
0.5979	Remote Similarity	NPD3133	Approved
0.5979	Remote Similarity	NPD3666	Approved
0.5979	Remote Similarity	NPD3665	Phase 1
0.5968	Remote Similarity	NPD6845	Suspended
0.5962	Remote Similarity	NPD5221	Approved
0.5962	Remote Similarity	NPD5222	Approved
0.5962	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4697	Phase 3
0.5943	Remote Similarity	NPD5285	Approved
0.5943	Remote Similarity	NPD5286	Approved
0.5943	Remote Similarity	NPD4696	Approved
0.593	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6052	Approved
0.5922	Remote Similarity	NPD7748	Approved
0.5913	Remote Similarity	NPD6274	Approved
0.5905	Remote Similarity	NPD4755	Approved
0.5905	Remote Similarity	NPD5173	Approved
0.5888	Remote Similarity	NPD5223	Approved
0.5887	Remote Similarity	NPD7260	Phase 2
0.5882	Remote Similarity	NPD7983	Approved
0.5877	Remote Similarity	NPD4632	Approved
0.5875	Remote Similarity	NPD9298	Approved
0.5872	Remote Similarity	NPD5141	Approved
0.5862	Remote Similarity	NPD6317	Approved
0.5859	Remote Similarity	NPD5279	Phase 3
0.5856	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5226	Approved
0.5833	Remote Similarity	NPD5225	Approved
0.5833	Remote Similarity	NPD4633	Approved
0.5833	Remote Similarity	NPD5224	Approved
0.5812	Remote Similarity	NPD6313	Approved
0.5812	Remote Similarity	NPD6335	Approved
0.5812	Remote Similarity	NPD6314	Approved
0.5794	Remote Similarity	NPD4700	Approved
0.5785	Remote Similarity	NPD7492	Approved
0.5784	Remote Similarity	NPD7838	Discovery
0.578	Remote Similarity	NPD5175	Approved
0.578	Remote Similarity	NPD5174	Approved
0.5776	Remote Similarity	NPD6868	Approved
0.5766	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD7518	Approved
0.5763	Remote Similarity	NPD7101	Approved
0.5763	Remote Similarity	NPD7100	Approved
0.5763	Remote Similarity	NPD7517	Approved
0.5763	Remote Similarity	NPD7519	Approved
0.5747	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6616	Approved
0.5738	Remote Similarity	NPD7507	Approved
0.5729	Remote Similarity	NPD4695	Discontinued
0.5728	Remote Similarity	NPD7515	Phase 2
0.5728	Remote Similarity	NPD7637	Suspended
0.5726	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD3198	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD6319	Approved
0.5714	Remote Similarity	NPD5654	Approved
0.5714	Remote Similarity	NPD6054	Approved
0.57	Remote Similarity	NPD6422	Discontinued
0.57	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD3702	Approved
0.5691	Remote Similarity	NPD7078	Approved
0.5688	Remote Similarity	NPD7632	Discontinued
0.5686	Remote Similarity	NPD4753	Phase 2
0.5684	Remote Similarity	NPD4802	Phase 2
0.5684	Remote Similarity	NPD4238	Approved
0.5673	Remote Similarity	NPD4202	Approved
0.5667	Remote Similarity	NPD6015	Approved
0.5667	Remote Similarity	NPD6016	Approved
0.5667	Remote Similarity	NPD5983	Phase 2
0.5645	Remote Similarity	NPD7736	Approved
0.5636	Remote Similarity	NPD4754	Approved
0.5625	Remote Similarity	NPD6412	Phase 2
0.5625	Remote Similarity	NPD6614	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data